N-(2-Furoyl)Glycine → Furan-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazine-1-yl]-ethyl}-amide

HRID 1178076

反応式

HRID 1178076 の反応式
CCN(C(C)C)C(C)C.[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:15]([NH:17][CH2:18][C:19]([OH:21])=O)=[O:16].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[N:45]1([C:51]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=2[C:59]([F:62])([F:61])[F:60])=[O:52])[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1>CN(C=O)C.O>[O:21]=[C:19]([N:48]1[CH2:49][CH2:50][N:45]([C:51](=[O:52])[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=2[C:59]([F:62])([F:60])[F:61])[CH2:46][CH2:47]1)[CH2:18][NH:17][C:15]([C:11]1[O:10][CH:14]=[CH:13][CH:12]=1)=[O:16]

参加物

8

反応物 5

HCID 21863N-(2-Furoyl)GlycineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 167337831-(2-Trifluoromethylbenzoyl)piperazine hydrochloride

生成物 1

HCID 59559660Furan-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazine-1-yl]-ethyl}-amide収率 33%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (0.143 mL, 0.83 mmol) was added to a stirred solution of [(furan-2-carbonyl)-amino]-acetic acid (40 mg, 0.24 mmol) in DMF (1 mL). HOBT (38 mg, 0.28 mmol), EDCI.HCl (54 mg, 0.28 mmol) were added, followed by the addition of piperazine-1-yl-(2-trifluoromethyl-phenyl)-methanone hydrochloride (0.2602 mmol) at room temperature. The resulting mixture was stirred at room temperature overnight. Water was then added, and the product was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification using column chromatography (using silica gel, 60-120 A° and 10% methanol in chloroform as the eluent) afforded furan-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazine-1-yl]-ethyl}-amide in 33% yield. LC-MS purity: 83%, 1H NMR (CDCl3): δ 7.74 (d, 1H), 7.60 (m, 2H), 7.56 (d, 2H), 7.48 (s, 1H), 7.12 (t, 1H), 6.50 (q, 1H), 4.30 (m, 2H), 4.08-3.82 (m, 2H), 3.78-3.64 (m, 2H), 3.62-3.48 (m, 2H), 3.22 (m, 2H).

後処理

  1. extractionthe product was extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude product
  6. customPurification

出典と根拠

ORDレコード
ord-47505f03ce0f49d981d333dcca6bfa28
出典データセット
uspto-grants-2010_11
特許番号
US07842696B2

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